# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd17117
_database_code_depnum_ccdc_archive 'CCDC 1537103'
_audit_update_record             
;
2017-03-10 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N O3 S'
_chemical_formula_weight         307.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.797(6)
_cell_length_b                   6.533(3)
_cell_length_c                   11.917(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.243(9)
_cell_angle_gamma                90
_cell_volume                     816.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1105
_cell_measurement_theta_min      6.600
_cell_measurement_theta_max      56.571

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4348
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.922
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             2747
_reflns_number_gt                2040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.900
_reflns_Friedel_fraction_full    0.877

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2747
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0891
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1649
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83537(18) -0.0750(3) 0.6807(2) 0.0501(6) Uani 1 1 d . . . . .
N1 N 0.9737(6) 0.0121(9) 0.7034(5) 0.0433(16) Uani 1 1 d . . . . .
O1 O 1.1761(5) 0.2286(8) 0.6962(5) 0.0590(16) Uani 1 1 d . . . . .
O2 O 0.8294(6) -0.2811(8) 0.6388(6) 0.0725(19) Uani 1 1 d . . . . .
O3 O 0.8229(5) -0.0290(9) 0.7895(5) 0.0662(18) Uani 1 1 d . . . . .
C1 C 1.1453(8) 0.0281(14) 0.6481(8) 0.058(2) Uani 1 1 d . . . . .
H1A H 1.1955 -0.0691 0.7138 0.070 Uiso 1 1 calc R U . . .
H1B H 1.1666 0.0111 0.5791 0.070 Uiso 1 1 calc R U . . .
C2 C 1.0059(8) -0.0153(12) 0.6019(7) 0.057(2) Uani 1 1 d . . . . .
H2A H 0.9554 0.0767 0.5332 0.068 Uiso 1 1 calc R U . . .
H2B H 0.9870 -0.1546 0.5707 0.068 Uiso 1 1 calc R U . . .
C3 C 1.0085(6) 0.2190(12) 0.7573(6) 0.0416(18) Uani 1 1 d . . . . .
H3A H 0.9903 0.2317 0.8286 0.050 Uiso 1 1 calc R U . . .
H3B H 0.9570 0.3191 0.6944 0.050 Uiso 1 1 calc R U . . .
C4 C 1.1480(7) 0.2634(12) 0.8001(7) 0.052(2) Uani 1 1 d . . . . .
C5 C 1.2383(9) 0.1383(15) 0.9106(8) 0.067(3) Uani 1 1 d . . . . .
H5 H 1.3205 0.1239 0.9196 0.080 Uiso 1 1 calc R U . . .
C6 C 1.2156(9) 0.0496(15) 0.9935(8) 0.067(3) Uani 1 1 d . . . . .
C7 C 1.2649(9) -0.069(2) 1.1079(8) 0.092(3) Uani 1 1 d . . . . .
H7A H 1.3198 -0.0015 1.1866 0.110 Uiso 1 1 calc R U . . .
H7B H 1.2843 -0.2126 1.1033 0.110 Uiso 1 1 calc R U . . .
C8 C 1.1300(10) -0.0041(15) 1.0404(8) 0.079(3) Uani 1 1 d . . . . .
H8A H 1.0664 -0.1076 0.9951 0.095 Uiso 1 1 calc R U . . .
H8B H 1.1019 0.1031 1.0783 0.095 Uiso 1 1 calc R U . . .
C9 C 1.1748(10) 0.4865(13) 0.8324(10) 0.084(3) Uani 1 1 d . . . . .
H9A H 1.1243 0.5678 0.7593 0.126 Uiso 1 1 calc R U . . .
H9B H 1.2636 0.5134 0.8596 0.126 Uiso 1 1 calc R U . . .
H9C H 1.1537 0.5208 0.8990 0.126 Uiso 1 1 calc R U . . .
C10 C 0.7225(7) 0.0669(13) 0.5536(8) 0.049(2) Uani 1 1 d . . . . .
C11 C 0.6852(7) 0.2561(13) 0.5747(8) 0.053(2) Uani 1 1 d . . . . .
H11 H 0.7153 0.3043 0.6568 0.063 Uiso 1 1 calc R U . . .
C12 C 0.6040(7) 0.3742(11) 0.4753(8) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.5767 0.4997 0.4908 0.069 Uiso 1 1 calc R U . . .
C13 C 0.5623(7) 0.3093(16) 0.3526(9) 0.060(2) Uani 1 1 d . . . . .
C14 C 0.6024(8) 0.1214(16) 0.3348(8) 0.066(3) Uani 1 1 d . . . . .
H14 H 0.5759 0.0749 0.2528 0.079 Uiso 1 1 calc R U . . .
C15 C 0.6804(8) -0.0005(13) 0.4333(8) 0.061(2) Uani 1 1 d . . . . .
H15 H 0.7044 -0.1290 0.4180 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4829(8) 0.449(2) 0.2433(9) 0.092(3) Uani 1 1 d . . . . .
H16A H 0.3945 0.4352 0.2227 0.138 Uiso 1 1 calc R U . . .
H16B H 0.4948 0.4128 0.1713 0.138 Uiso 1 1 calc R U . . .
H16C H 0.5092 0.5885 0.2665 0.138 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.403(6) . ?
S1 O2 1.427(6) . ?
S1 N1 1.629(7) . ?
S1 C10 1.755(8) . ?
N1 C2 1.435(9) . ?
N1 C3 1.472(9) . ?
O1 C1 1.409(10) . ?
O1 C4 1.440(10) . ?
C1 C2 1.504(11) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.511(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.501(11) . ?
C4 C9 1.504(12) . ?
C5 C6 1.274(12) . ?
C5 H5 0.9300 . ?
C6 C8 1.405(14) . ?
C6 C7 1.441(13) . ?
C7 C8 1.480(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.358(10) . ?
C10 C11 1.373(11) . ?
C11 C12 1.370(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(14) . ?
C13 C16 1.515(13) . ?
C14 C15 1.368(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 121.1(4) . . ?
O3 S1 N1 107.0(3) . . ?
O2 S1 N1 105.8(4) . . ?
O3 S1 C10 109.0(4) . . ?
O2 S1 C10 107.5(4) . . ?
N1 S1 C10 105.4(3) . . ?
C2 N1 C3 110.7(6) . . ?
C2 N1 S1 116.6(5) . . ?
C3 N1 S1 116.8(5) . . ?
C1 O1 C4 112.3(6) . . ?
O1 C1 C2 111.0(7) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N1 C2 C1 109.6(6) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 111.5(6) . . ?
N1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C5 108.6(7) . . ?
O1 C4 C9 105.6(7) . . ?
C5 C4 C9 108.8(7) . . ?
O1 C4 C3 108.9(6) . . ?
C5 C4 C3 114.7(7) . . ?
C9 C4 C3 110.0(8) . . ?
C6 C5 C4 127.7(9) . . ?
C6 C5 H5 116.2 . . ?
C4 C5 H5 116.2 . . ?
C5 C6 C8 150.0(10) . . ?
C5 C6 C7 147.4(10) . . ?
C8 C6 C7 62.7(7) . . ?
C6 C7 C8 57.5(6) . . ?
C6 C7 H7A 118.0 . . ?
C8 C7 H7A 118.0 . . ?
C6 C7 H7B 118.0 . . ?
C8 C7 H7B 118.0 . . ?
H7A C7 H7B 115.2 . . ?
C6 C8 C7 59.9(7) . . ?
C6 C8 H8A 117.8 . . ?
C7 C8 H8A 117.8 . . ?
C6 C8 H8B 117.8 . . ?
C7 C8 H8B 117.8 . . ?
H8A C8 H8B 114.9 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.5(8) . . ?
C15 C10 S1 120.4(6) . . ?
C11 C10 S1 119.9(6) . . ?
C12 C11 C10 120.3(8) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.8(8) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.4(8) . . ?
C14 C13 C16 122.0(10) . . ?
C12 C13 C16 120.5(10) . . ?
C15 C14 C13 122.2(9) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C10 C15 C14 119.7(8) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C2 -178.9(5) . . . . ?
O2 S1 N1 C2 50.7(6) . . . . ?
C10 S1 N1 C2 -63.0(6) . . . . ?
O3 S1 N1 C3 -44.8(6) . . . . ?
O2 S1 N1 C3 -175.2(5) . . . . ?
C10 S1 N1 C3 71.1(6) . . . . ?
C4 O1 C1 C2 59.7(8) . . . . ?
C3 N1 C2 C1 56.1(8) . . . . ?
S1 N1 C2 C1 -167.1(5) . . . . ?
O1 C1 C2 N1 -58.4(9) . . . . ?
C2 N1 C3 C4 -55.8(8) . . . . ?
S1 N1 C3 C4 167.5(5) . . . . ?
C1 O1 C4 C5 68.4(8) . . . . ?
C1 O1 C4 C9 -175.1(7) . . . . ?
C1 O1 C4 C3 -57.1(8) . . . . ?
N1 C3 C4 O1 54.5(8) . . . . ?
N1 C3 C4 C5 -67.3(9) . . . . ?
N1 C3 C4 C9 169.8(7) . . . . ?
O1 C4 C5 C6 -144.8(9) . . . . ?
C9 C4 C5 C6 100.8(11) . . . . ?
C3 C4 C5 C6 -22.8(14) . . . . ?
C4 C5 C6 C8 3(3) . . . . ?
C4 C5 C6 C7 -176.8(15) . . . . ?
C5 C6 C7 C8 -179.9(19) . . . . ?
C5 C6 C8 C7 180(2) . . . . ?
O3 S1 C10 C15 -154.9(7) . . . . ?
O2 S1 C10 C15 -21.9(8) . . . . ?
N1 S1 C10 C15 90.6(7) . . . . ?
O3 S1 C10 C11 31.2(7) . . . . ?
O2 S1 C10 C11 164.1(6) . . . . ?
N1 S1 C10 C11 -83.3(7) . . . . ?
C15 C10 C11 C12 1.4(12) . . . . ?
S1 C10 C11 C12 175.4(6) . . . . ?
C10 C11 C12 C13 -2.5(12) . . . . ?
C11 C12 C13 C14 1.6(12) . . . . ?
C11 C12 C13 C16 -174.1(8) . . . . ?
C12 C13 C14 C15 0.4(13) . . . . ?
C16 C13 C14 C15 176.0(8) . . . . ?
C11 C10 C15 C14 0.6(12) . . . . ?
S1 C10 C15 C14 -173.4(7) . . . . ?
C13 C14 C15 C10 -1.5(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O1 0.93 2.54 3.283(10) 136.8 2_746
C15 H15 O1 0.93 2.54 3.283(10) 136.8 2_746
C15 H15 O1 0.93 2.54 3.283(10) 136.8 2_746

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mj22137_0m
_database_code_depnum_ccdc_archive 'CCDC 2178224'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;
_audit_creation_date             2022-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H26 N O3 S'
_chemical_formula_sum            'C18 H26 N O3 S'
_chemical_formula_weight         336.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7615(3)
_cell_length_b                   7.0280(2)
_cell_length_c                   21.1943(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.4420(10)
_cell_angle_gamma                90
_cell_volume                     1748.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    213
_cell_measurement_theta_max      54.770
_cell_measurement_theta_min      5.773
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    1.142
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1825 before and 0.1018 after correction. The Ratio of minimum to maximum transmission is 0.5614. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16374
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.618
_diffrn_reflns_theta_max         55.082
_diffrn_reflns_theta_min         3.842
_diffrn_ambient_temperature      213.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3418
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2730
_reflns_number_total             3302
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1080P)²+0.8215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2B,H2A), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50587(5) 0.76108(10) 0.33344(3) 0.0492(3) Uani 1 1 d . . . . .
O1 O 0.35980(13) 0.5034(2) 0.15617(7) 0.0430(4) Uani 1 1 d . . . . .
O2 O 0.62648(17) 0.7367(3) 0.33665(10) 0.0676(6) Uani 1 1 d . . . . .
O3 O 0.4572(2) 0.9448(3) 0.34121(10) 0.0677(6) Uani 1 1 d . . . . .
N1 N 0.45912(16) 0.6836(3) 0.26368(9) 0.0398(5) Uani 1 1 d . . . . .
H1 H 0.499330 0.765026 0.234097 0.048 Uiso 1 1 calc R . . . .
C1 C 0.47615(18) 0.4592(3) 0.17634(10) 0.0367(5) Uani 1 1 d . . . . .
C2 C 0.49429(19) 0.4907(3) 0.24727(10) 0.0386(5) Uani 1 1 d . . . . .
H2B H 0.449765 0.397557 0.269770 0.046 Uiso 1 1 calc R . . . .
H2A H 0.574901 0.472526 0.260338 0.046 Uiso 1 1 calc R . . . .
C3 C 0.3390(2) 0.7157(4) 0.24522(13) 0.0453(6) Uani 1 1 d . . . . .
H3A H 0.316942 0.845315 0.256416 0.054 Uiso 1 1 calc R . . . .
H3B H 0.291347 0.625858 0.267145 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3232(2) 0.6871(4) 0.17421(12) 0.0482(6) Uani 1 1 d . . . . .
H4A H 0.242584 0.703243 0.160789 0.058 Uiso 1 1 calc R . . . .
H4B H 0.366772 0.783898 0.152770 0.058 Uiso 1 1 calc R . . . .
C5 C 0.5593(2) 0.5781(3) 0.14177(12) 0.0433(6) Uani 1 1 d . . . . .
C6 C 0.6817(2) 0.6328(4) 0.15846(15) 0.0606(8) Uani 1 1 d . . . . .
H6A H 0.734450 0.524842 0.161649 0.073 Uiso 1 1 calc R . . . .
H6B H 0.691970 0.716907 0.195226 0.073 Uiso 1 1 calc R . . . .
C7 C 0.6784(3) 0.7370(4) 0.09422(17) 0.0672(9) Uani 1 1 d . . . . .
H7A H 0.687295 0.875349 0.097370 0.081 Uiso 1 1 calc R . . . .
H7B H 0.728377 0.682362 0.063604 0.081 Uiso 1 1 calc R . . . .
C8 C 0.5556(3) 0.6696(5) 0.08677(14) 0.0601(7) Uani 1 1 d . . . . .
H8 H 0.497753 0.686603 0.054716 0.072 Uiso 1 1 calc R . . . .
C9 C 0.4851(2) 0.2435(3) 0.16145(12) 0.0442(6) Uani 1 1 d . . . . .
H9 H 0.416529 0.182222 0.177193 0.053 Uiso 1 1 calc R . . . .
C10 C 0.5873(2) 0.1469(4) 0.19438(15) 0.0572(7) Uani 1 1 d . . . . .
H10A H 0.656629 0.204301 0.180657 0.086 Uiso 1 1 calc GR . . . .
H10B H 0.586425 0.012551 0.183837 0.086 Uiso 1 1 calc GR . . . .
H10C H 0.584314 0.161824 0.239751 0.086 Uiso 1 1 calc GR . . . .
C11 C 0.4821(3) 0.2076(4) 0.09030(13) 0.0555(7) Uani 1 1 d . . . . .
H11A H 0.419798 0.278786 0.069610 0.083 Uiso 1 1 calc GR . . . .
H11B H 0.471118 0.072891 0.082095 0.083 Uiso 1 1 calc GR . . . .
H11C H 0.553486 0.248391 0.074014 0.083 Uiso 1 1 calc GR . . . .
C12 C 0.44985(19) 0.6034(4) 0.38788(11) 0.0425(6) Uani 1 1 d . . . . .
C13 C 0.3440(2) 0.6370(4) 0.41163(11) 0.0472(6) Uani 1 1 d . . . . .
H13 H 0.304480 0.750567 0.402039 0.057 Uiso 1 1 calc R . . . .
C14 C 0.2980(2) 0.5008(4) 0.44951(12) 0.0513(7) Uani 1 1 d . . . . .
H14 H 0.226498 0.523471 0.465639 0.062 Uiso 1 1 calc R . . . .
C15 C 0.3539(2) 0.3320(4) 0.46446(11) 0.0492(6) Uani 1 1 d . . . . .
C16 C 0.4597(2) 0.3034(4) 0.44115(12) 0.0535(7) Uani 1 1 d . . . . .
H16 H 0.499319 0.190065 0.451067 0.064 Uiso 1 1 calc R . . . .
C17 C 0.5084(2) 0.4366(4) 0.40384(12) 0.0515(7) Uani 1 1 d . . . . .
H17 H 0.581108 0.415115 0.389113 0.062 Uiso 1 1 calc R . . . .
C18 C 0.2997(3) 0.1817(5) 0.50308(15) 0.0718(9) Uani 1 1 d . . . . .
H18A H 0.258480 0.241759 0.536018 0.108 Uiso 1 1 calc GR . . . .
H18B H 0.358277 0.099229 0.522141 0.108 Uiso 1 1 calc GR . . . .
H18C H 0.247300 0.107152 0.476021 0.108 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.427(2) . ?
S1 O3 1.426(2) . ?
S1 N1 1.639(2) . ?
S1 C12 1.756(3) . ?
O1 C1 1.443(3) . ?
O1 C4 1.420(3) . ?
N1 C2 1.465(3) . ?
N1 C3 1.461(3) . ?
C1 C2 1.522(3) . ?
C1 C5 1.509(3) . ?
C1 C9 1.553(3) . ?
C3 C4 1.519(4) . ?
C5 C6 1.511(4) . ?
C5 C8 1.330(4) . ?
C6 C7 1.544(5) . ?
C7 C8 1.518(4) . ?
C9 C10 1.514(4) . ?
C9 C11 1.527(4) . ?
C12 C13 1.391(3) . ?
C12 C17 1.391(4) . ?
C13 C14 1.380(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.381(4) . ?
C15 C18 1.501(4) . ?
C16 C17 1.372(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 106.37(11) . . ?
O2 S1 C12 107.70(13) . . ?
O3 S1 O2 120.55(13) . . ?
O3 S1 N1 106.84(12) . . ?
O3 S1 C12 109.07(12) . . ?
N1 S1 C12 105.31(11) . . ?
C4 O1 C1 114.42(18) . . ?
C2 N1 S1 115.93(16) . . ?
C3 N1 S1 117.18(16) . . ?
C3 N1 C2 111.22(19) . . ?
O1 C1 C2 109.60(17) . . ?
O1 C1 C5 111.56(19) . . ?
O1 C1 C9 102.99(18) . . ?
C2 C1 C9 109.61(19) . . ?
C5 C1 C2 110.03(19) . . ?
C5 C1 C9 112.83(19) . . ?
N1 C2 C1 110.15(19) . . ?
N1 C3 C4 107.69(19) . . ?
O1 C4 C3 111.5(2) . . ?
C1 C5 C6 131.5(2) . . ?
C8 C5 C1 134.9(3) . . ?
C8 C5 C6 93.6(2) . . ?
C5 C6 C7 86.6(2) . . ?
C8 C7 C6 85.3(2) . . ?
C5 C8 C7 94.5(3) . . ?
C10 C9 C1 114.0(2) . . ?
C10 C9 C11 110.6(2) . . ?
C11 C9 C1 111.3(2) . . ?
C13 C12 S1 120.6(2) . . ?
C13 C12 C17 119.7(3) . . ?
C17 C12 S1 119.47(19) . . ?
C14 C13 C12 118.9(2) . . ?
C13 C14 C15 122.0(2) . . ?
C14 C15 C18 121.1(3) . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 C18 120.9(3) . . ?
C17 C16 C15 121.5(3) . . ?
C16 C17 C12 119.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v22047_0m
_database_code_depnum_ccdc_archive 'CCDC 2178226'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 Cl N2 O6 S'
_chemical_formula_weight         492.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5010(10)
_cell_length_b                   7.4457(11)
_cell_length_c                   24.493(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.467(6)
_cell_angle_gamma                90
_cell_volume                     1180.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3368
_cell_measurement_theta_min      5.012
_cell_measurement_theta_max      46.122

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.292
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10759
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 1.002
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4110
_reflns_number_gt                3045
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     1.004
_reflns_Friedel_fraction_full    0.980

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1576P)²+1.7098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4110
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2793
_refine_ls_wR_factor_gt          0.2520
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.5662(5) 0.8386(6) 0.05722(14) 0.0735(11) Uani 1 1 d . . . . .
S1 S 0.1453(4) 0.2227(4) 0.19097(11) 0.0451(7) Uani 1 1 d . . . . .
O1 O 0.4300(13) 0.6717(12) 0.2510(3) 0.056(2) Uani 1 1 d . . . . .
O2 O 0.1607(15) 0.7091(17) 0.3010(4) 0.074(3) Uani 1 1 d . . . . .
O3 O 1.066(2) 0.439(3) 0.4781(6) 0.122(6) Uani 1 1 d . . . . .
O4 O 0.805(3) 0.452(3) 0.5268(6) 0.139(7) Uani 1 1 d . . . . .
O5 O 0.2537(17) 0.1750(13) 0.1453(4) 0.073(3) Uani 1 1 d . . . . .
O6 O -0.0513(17) 0.1397(13) 0.1980(4) 0.076(3) Uani 1 1 d . . . . .
N1 N 0.0964(13) 0.4393(12) 0.1899(4) 0.042(2) Uani 1 1 d . . . . .
N2 N 0.879(3) 0.472(2) 0.4837(5) 0.094(5) Uani 1 1 d . . . . .
C1 C -0.110(2) 0.5137(16) 0.1901(5) 0.051(3) Uani 1 1 d . . . . .
H1A H -0.1055 0.6175 0.2141 0.061 Uiso 1 1 calc R U . . .
H1B H -0.2002 0.4249 0.2043 0.061 Uiso 1 1 calc R U . . .
C2 C -0.1976(16) 0.5691(15) 0.1329(4) 0.041(2) Uani 1 1 d . . . . .
C3 C -0.2219(16) 0.7390(16) 0.1213(4) 0.044(2) Uani 1 1 d . . . . .
H3 H -0.1979 0.8194 0.1503 0.053 Uiso 1 1 calc R U . . .
C4 C -0.2854(15) 0.8184(13) 0.0653(4) 0.038(2) Uani 1 1 d . . . . .
C5 C -0.189(3) 0.7779(19) 0.0170(5) 0.069(4) Uani 1 1 d . . . . .
H5A H -0.2770 0.7633 -0.0170 0.083 Uiso 1 1 calc R U . . .
H5B H -0.0669 0.7025 0.0206 0.083 Uiso 1 1 calc R U . . .
C6 C -0.174(3) 0.960(2) 0.0422(6) 0.072(4) Uani 1 1 d . . . . .
H6A H -0.0425 0.9958 0.0612 0.086 Uiso 1 1 calc R U . . .
H6B H -0.2526 1.0566 0.0236 0.086 Uiso 1 1 calc R U . . .
C7 C -0.237(2) 0.4173(17) 0.0920(5) 0.060(3) Uani 1 1 d . . . . .
H7A H -0.3530 0.3479 0.1012 0.090 Uiso 1 1 calc R U . . .
H7B H -0.1167 0.3416 0.0932 0.090 Uiso 1 1 calc R U . . .
H7C H -0.2649 0.4660 0.0558 0.090 Uiso 1 1 calc R U . . .
C8 C 0.2587(17) 0.5539(16) 0.1677(5) 0.047(3) Uani 1 1 d . . . . .
H8A H 0.3835 0.4833 0.1664 0.056 Uiso 1 1 calc R U . . .
H8B H 0.2116 0.5887 0.1304 0.056 Uiso 1 1 calc R U . . .
C9 C 0.309(2) 0.7184(19) 0.2005(5) 0.057(3) Uani 1 1 d . . . . .
H9A H 0.3859 0.8012 0.1796 0.069 Uiso 1 1 calc R U . . .
H9B H 0.1822 0.7772 0.2086 0.069 Uiso 1 1 calc R U . . .
C10 C 0.337(2) 0.6755(16) 0.2981(5) 0.053(3) Uani 1 1 d . . . . .
C11 C 0.486(2) 0.6239(18) 0.3463(5) 0.055(3) Uani 1 1 d . . . . .
C12 C 0.417(2) 0.631(3) 0.3968(6) 0.076(4) Uani 1 1 d . . . . .
H12 H 0.2836 0.6696 0.4007 0.092 Uiso 1 1 calc R U . . .
C13 C 0.547(3) 0.579(3) 0.4433(6) 0.083(5) Uani 1 1 d . . . . .
H13 H 0.4991 0.5786 0.4779 0.100 Uiso 1 1 calc R U . . .
C14 C 0.742(3) 0.529(2) 0.4365(5) 0.068(4) Uani 1 1 d . . . . .
C15 C 0.827(2) 0.531(2) 0.3847(6) 0.068(4) Uani 1 1 d . . . . .
H15 H 0.9639 0.5020 0.3809 0.081 Uiso 1 1 calc R U . . .
C16 C 0.689(2) 0.581(2) 0.3404(5) 0.062(3) Uani 1 1 d . . . . .
H16 H 0.7351 0.5852 0.3057 0.074 Uiso 1 1 calc R U . . .
C17 C 0.3092(18) 0.1841(15) 0.2506(5) 0.049(3) Uani 1 1 d . . . . .
C18 C 0.237(3) 0.206(2) 0.3013(6) 0.072(4) Uani 1 1 d . . . . .
H18 H 0.1044 0.2495 0.3036 0.087 Uiso 1 1 calc R U . . .
C19 C 0.361(3) 0.163(2) 0.3495(6) 0.081(5) Uani 1 1 d . . . . .
H19 H 0.3087 0.1727 0.3835 0.098 Uiso 1 1 calc R U . . .
C20 C 0.563(3) 0.105(2) 0.3457(7) 0.081(5) Uani 1 1 d . . . . .
C21 C 0.637(2) 0.085(2) 0.2953(8) 0.080(5) Uani 1 1 d . . . . .
H21 H 0.7699 0.0414 0.2932 0.096 Uiso 1 1 calc R U . . .
C22 C 0.513(2) 0.1289(17) 0.2468(6) 0.064(4) Uani 1 1 d . . . . .
H22 H 0.5653 0.1213 0.2128 0.076 Uiso 1 1 calc R U . . .
C23 C 0.703(4) 0.057(3) 0.3963(8) 0.123(9) Uani 1 1 d . . . . .
H23A H 0.6234 0.0489 0.4272 0.185 Uiso 1 1 calc R U . . .
H23B H 0.8066 0.1489 0.4030 0.185 Uiso 1 1 calc R U . . .
H23C H 0.7689 -0.0557 0.3908 0.185 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.823(10) . ?
S1 O5 1.422(10) . ?
S1 O6 1.445(10) . ?
S1 N1 1.644(9) . ?
S1 C17 1.747(12) . ?
O1 C10 1.353(14) . ?
O1 C9 1.444(14) . ?
O2 C10 1.180(15) . ?
O3 N2 1.26(2) . ?
O4 N2 1.209(18) . ?
N1 C1 1.453(15) . ?
N1 C8 1.499(13) . ?
N2 C14 1.45(2) . ?
C1 C2 1.518(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.303(16) . ?
C2 C7 1.515(15) . ?
C3 C4 1.513(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(15) . ?
C4 C6 1.429(17) . ?
C5 C6 1.49(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.484(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(19) . ?
C11 C12 1.356(18) . ?
C11 C16 1.38(2) . ?
C12 C13 1.40(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.35(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.430(19) . ?
C15 C16 1.39(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.378(18) . ?
C17 C22 1.397(18) . ?
C18 C19 1.40(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.39(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.38(3) . ?
C20 C23 1.51(2) . ?
C21 C22 1.41(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O6 119.9(6) . . ?
O5 S1 N1 110.0(6) . . ?
O6 S1 N1 104.4(6) . . ?
O5 S1 C17 107.9(6) . . ?
O6 S1 C17 107.8(6) . . ?
N1 S1 C17 106.1(5) . . ?
C10 O1 C9 118.2(10) . . ?
C1 N1 C8 117.8(9) . . ?
C1 N1 S1 123.5(8) . . ?
C8 N1 S1 115.0(7) . . ?
O4 N2 O3 122.6(17) . . ?
O4 N2 C14 117.8(18) . . ?
O3 N2 C14 119.5(14) . . ?
N1 C1 C2 111.4(9) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C7 124.9(10) . . ?
C3 C2 C1 119.4(9) . . ?
C7 C2 C1 115.6(10) . . ?
C2 C3 C4 126.4(10) . . ?
C2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C5 C4 C6 63.0(10) . . ?
C5 C4 C3 124.6(10) . . ?
C6 C4 C3 122.9(10) . . ?
C5 C4 Cl1 116.2(9) . . ?
C6 C4 Cl1 115.9(9) . . ?
C3 C4 Cl1 108.3(7) . . ?
C4 C5 C6 58.6(8) . . ?
C4 C5 H5A 117.9 . . ?
C6 C5 H5A 117.9 . . ?
C4 C5 H5B 117.9 . . ?
C6 C5 H5B 117.9 . . ?
H5A C5 H5B 115.1 . . ?
C4 C6 C5 58.4(8) . . ?
C4 C6 H6A 117.9 . . ?
C5 C6 H6A 117.9 . . ?
C4 C6 H6B 117.9 . . ?
C5 C6 H6B 117.9 . . ?
H6A C6 H6B 115.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 113.5(9) . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
N1 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C8 109.9(11) . . ?
O1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O1 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 O1 124.8(12) . . ?
O2 C10 C11 124.3(11) . . ?
O1 C10 C11 110.8(11) . . ?
C12 C11 C16 120.5(13) . . ?
C12 C11 C10 117.4(12) . . ?
C16 C11 C10 122.0(11) . . ?
C11 C12 C13 120.3(15) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.3(14) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 123.5(14) . . ?
C13 C14 N2 119.5(14) . . ?
C15 C14 N2 116.9(15) . . ?
C16 C15 C14 114.9(13) . . ?
C16 C15 H15 122.5 . . ?
C14 C15 H15 122.5 . . ?
C11 C16 C15 122.2(12) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C18 C17 C22 120.0(12) . . ?
C18 C17 S1 120.1(10) . . ?
C22 C17 S1 119.9(10) . . ?
C17 C18 C19 121.2(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 118.7(15) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C21 C20 C19 120.5(14) . . ?
C21 C20 C23 118(2) . . ?
C19 C20 C23 121.1(19) . . ?
C20 C21 C22 120.7(16) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 118.8(15) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 S1 N1 C1 123.9(9) . . . . ?
O6 S1 N1 C1 -5.9(10) . . . . ?
C17 S1 N1 C1 -119.7(9) . . . . ?
O5 S1 N1 C8 -34.0(9) . . . . ?
O6 S1 N1 C8 -163.8(8) . . . . ?
C17 S1 N1 C8 82.4(9) . . . . ?
C8 N1 C1 C2 57.3(13) . . . . ?
S1 N1 C1 C2 -100.0(11) . . . . ?
N1 C1 C2 C3 -110.4(12) . . . . ?
N1 C1 C2 C7 65.5(14) . . . . ?
C7 C2 C3 C4 -2.3(18) . . . . ?
C1 C2 C3 C4 173.2(10) . . . . ?
C2 C3 C4 C5 -51.3(17) . . . . ?
C2 C3 C4 C6 -129.1(13) . . . . ?
C2 C3 C4 Cl1 91.2(12) . . . . ?
C3 C4 C5 C6 -112.9(13) . . . . ?
Cl1 C4 C5 C6 107.2(11) . . . . ?
C3 C4 C6 C5 115.4(13) . . . . ?
Cl1 C4 C6 C5 -107.7(11) . . . . ?
C1 N1 C8 C9 64.6(13) . . . . ?
S1 N1 C8 C9 -136.2(9) . . . . ?
C10 O1 C9 C8 -105.8(12) . . . . ?
N1 C8 C9 O1 74.0(13) . . . . ?
C9 O1 C10 O2 2.4(19) . . . . ?
C9 O1 C10 C11 -179.8(10) . . . . ?
O2 C10 C11 C12 -5(2) . . . . ?
O1 C10 C11 C12 176.8(12) . . . . ?
O2 C10 C11 C16 178.1(14) . . . . ?
O1 C10 C11 C16 0.2(17) . . . . ?
C16 C11 C12 C13 -5(2) . . . . ?
C10 C11 C12 C13 178.0(15) . . . . ?
C11 C12 C13 C14 2(3) . . . . ?
C12 C13 C14 C15 2(3) . . . . ?
C12 C13 C14 N2 -179.1(16) . . . . ?
O4 N2 C14 C13 8(3) . . . . ?
O3 N2 C14 C13 -174.6(18) . . . . ?
O4 N2 C14 C15 -172.8(18) . . . . ?
O3 N2 C14 C15 4(2) . . . . ?
C13 C14 C15 C16 -3(2) . . . . ?
N2 C14 C15 C16 178.0(14) . . . . ?
C12 C11 C16 C15 4(2) . . . . ?
C10 C11 C16 C15 -179.3(13) . . . . ?
C14 C15 C16 C11 0(2) . . . . ?
O5 S1 C17 C18 -174.8(10) . . . . ?
O6 S1 C17 C18 -44.1(12) . . . . ?
N1 S1 C17 C18 67.3(11) . . . . ?
O5 S1 C17 C22 4.3(11) . . . . ?
O6 S1 C17 C22 135.0(10) . . . . ?
N1 S1 C17 C22 -113.6(10) . . . . ?
C22 C17 C18 C19 -4(2) . . . . ?
S1 C17 C18 C19 175.2(12) . . . . ?
C17 C18 C19 C20 3(2) . . . . ?
C18 C19 C20 C21 -2(2) . . . . ?
C18 C19 C20 C23 179.9(15) . . . . ?
C19 C20 C21 C22 3(2) . . . . ?
C23 C20 C21 C22 -179.4(14) . . . . ?
C18 C17 C22 C21 4.1(19) . . . . ?
S1 C17 C22 C21 -175.0(10) . . . . ?
C20 C21 C22 C17 -4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655
C22 H22 O6 0.93 2.56 3.179(19) 124.8 1_655

_refine_diff_density_max         0.979
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

